Bregman Leaves Red Sox to Sign 5-Yr, $175 Million Deal with Cubs

After only one season at Fenway Park, third baseman Alex Bregman has signed a 5-year, $175 million contract with the Chicago Cubs.

Bregman, 31, played his first 9 MLB seasons with the Houston Astros earning two World Series rings in 2017 and in 2022. Prior to the 2025 season, Bregman signed a 3-year, $120 million deal with the Boston Red Sox. 

Although he was named to the AL All-Star Team, Bregman did miss more than two months of the season due to a right quad injury. In 114 games in 2025, Bregman hit .273 with 18 HR and 62 RBI as the Red Sox reached the post-season for the first time since 2021.

However, Bregman would opt out of his Red Sox contract back in early November. I think a reasonable case can be made that signing Bregman did long term damage to the Red Sox. His addition caused the kerfuffle with Rafael Devers who had been under contract until 2033 only to trade him to the San Francisco Giants in mid-June. The Red Sox forced Devers to move from third to DH and then to first base to make room for Bregman only to be gone after a single season and find another third baseman. Was it worth all that? Will having hastily traded Devers last year bite the Red Sox in the ass?

So, who plays third for the Red Sox in 2026? Do they sign longtime Blue Jay Bo Bichette? Do they make yet another deal with the St. Louis Cardinals and acquire Brendan Donovan? The Bosox acquired both pitcher Sonny Gray and first baseman Wilson Contreras from the Redbirds this offseason. Or do they stay in-house and let Marcelo Mayer, Nate Eaton, Romy Gonzalez and Tristan Gray fight it out?

Moving onto Wrigley, does Bregman taking over third force the Cubs to ship out Matt Shaw or Nico Hoerner? While Bregman is valued for his leadership one does wonder if he can stay healthy in the long run. Don't get me wrong. I understand why the Cubs added him. The Cubs reached the post-season for the first time in five years and think they can make a deeper run with Bregman on the team. That being said, the Red Sox were eliminated in the ALWC round by the New York Yankees. So, who can say if Bregman will actually improve the team? Then again Bregman's departure might not serve the Red Sox will either.